NO315321B1 - Nye 2-(iminometyl)amino-fenylderivater, fremstilling og anvendelse derav, samt farmasoytisk preparat - Google Patents

Nye 2-(iminometyl)amino-fenylderivater, fremstilling og anvendelse derav, samt farmasoytisk preparat Download PDF

Info

Publication number: NO315321B1
Authority: NO; Norway
Prior art keywords: general formula; methyl; thienyl; imino; amino
Prior art date: 1997-06-20

Application number

NO19996208A

Other languages

English (en)

Norwegian (no)

Other versions

NO996208D0 (no

NO996208L (no

Inventor

Jeremiah Harnett

Dennis Bigg

De Lassauniere Pierre Chabrier

Serge Auvin

Original Assignee

Sod Conseils Rech Applic

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-06-20

Filing date

1999-12-15

Publication date

2003-08-18

1999-12-15 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

1999-12-15 Publication of NO996208D0 publication Critical patent/NO996208D0/no

2000-02-15 Publication of NO996208L publication Critical patent/NO996208L/no

2003-08-18 Publication of NO315321B1 publication Critical patent/NO315321B1/no

Links

-1 2- (iminomethyl) amino-phenyl Chemical class 0.000 title claims description 82
238000002360 preparation method Methods 0.000 title claims description 12
239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 76
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 75
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 73
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 71
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
150000001412 amines Chemical group 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 32
238000009833 condensation Methods 0.000 claims description 28
230000005494 condensation Effects 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 28
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 26
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 24
125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 20
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 16
230000002378 acidificating effect Effects 0.000 claims description 14
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 12
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 12
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
230000003859 lipid peroxidation Effects 0.000 claims description 10
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 8
108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
208000023105 Huntington disease Diseases 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 4
125000006000 trichloroethyl group Chemical group 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
239000000543 intermediate Substances 0.000 description 236
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 111
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 75
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
238000002844 melting Methods 0.000 description 64
230000008018 melting Effects 0.000 description 64
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
239000000843 powder Substances 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 44
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 43
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
230000015572 biosynthetic process Effects 0.000 description 38
239000000047 product Substances 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
238000003786 synthesis reaction Methods 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 34
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
150000001409 amidines Chemical class 0.000 description 24
239000012074 organic phase Substances 0.000 description 23
239000007787 solid Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
229930192474 thiophene Natural products 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
150000001408 amides Chemical class 0.000 description 17
239000012267 brine Substances 0.000 description 17
239000003480 eluent Substances 0.000 description 17
239000003921 oil Substances 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
238000001035 drying Methods 0.000 description 16
239000013067 intermediate product Substances 0.000 description 16
239000002585 base Substances 0.000 description 15
238000000034 method Methods 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
239000000377 silicon dioxide Substances 0.000 description 13
238000011282 treatment Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000003857 carboxamides Chemical class 0.000 description 12
150000001735 carboxylic acids Chemical class 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
238000010908 decantation Methods 0.000 description 11
230000000694 effects Effects 0.000 description 11
238000001914 filtration Methods 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
235000013877 carbamide Nutrition 0.000 description 10
238000000746 purification Methods 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000010647 peptide synthesis reaction Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
241000700159 Rattus Species 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
150000001448 anilines Chemical class 0.000 description 7
150000002513 isocyanates Chemical class 0.000 description 7
235000015320 potassium carbonate Nutrition 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000012429 reaction media Substances 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
238000013019 agitation Methods 0.000 description 6
239000004202 carbamide Substances 0.000 description 6
239000006260 foam Substances 0.000 description 6
239000012458 free base Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
239000012047 saturated solution Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
SNGMJMWZOCFLSK-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-3-(4-nitrophenyl)-1,3-thiazolidin-4-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(C(=O)CS2)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 SNGMJMWZOCFLSK-UHFFFAOYSA-N 0.000 description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229940118019 malondialdehyde Drugs 0.000 description 5
150000003138 primary alcohols Chemical class 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 4
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 4
WLHISESTWLOVMB-UHFFFAOYSA-N 4-(1,3-thiazolidin-3-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CSCC1 WLHISESTWLOVMB-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
SLNWZAKZOMMXGJ-UHFFFAOYSA-N I.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(NC(=O)C=2OC(=CC=2)C=2C=CC(=CC=2)N(C=N)C=2SC=CC=2)=C1 Chemical compound I.CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(NC(=O)C=2OC(=CC=2)C=2C=CC(=CC=2)N(C=N)C=2SC=CC=2)=C1 SLNWZAKZOMMXGJ-UHFFFAOYSA-N 0.000 description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
208000002193 Pain Diseases 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
210000003710 cerebral cortex Anatomy 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
150000002460 imidazoles Chemical class 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
150000002547 isoxazolines Chemical class 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 4
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
FCGKUUOTWLWJHE-UHFFFAOYSA-N 2,6-ditert-butyl-4-nitrophenol Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC(C(C)(C)C)=C1O FCGKUUOTWLWJHE-UHFFFAOYSA-N 0.000 description 3
125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 3
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
MNDTVJMRXYKBPV-UHFFFAOYSA-N 4-amino-2,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(N)=CC(C(C)(C)C)=C1O MNDTVJMRXYKBPV-UHFFFAOYSA-N 0.000 description 3
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000007995 HEPES buffer Substances 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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SGQPXIZHVCLLRP-ZDUSSCGKSA-N tert-butyl (3s)-3-(4-nitrophenoxy)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1OC1=CC=C([N+]([O-])=O)C=C1 SGQPXIZHVCLLRP-ZDUSSCGKSA-N 0.000 description 1
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OKIPVLDHIDUTOG-UHFFFAOYSA-N tert-butyl 3-amino-4-(1-benzhydrylazetidin-3-yl)oxybenzoate Chemical compound NC1=CC(C(=O)OC(C)(C)C)=CC=C1OC1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 OKIPVLDHIDUTOG-UHFFFAOYSA-N 0.000 description 1
ZVUQAXUPDWVVQL-UHFFFAOYSA-N tert-butyl 3-amino-4-[1-(2-hydroxy-5-methoxybenzoyl)azetidin-3-yl]oxybenzoate Chemical compound COC1=CC=C(O)C(C(=O)N2CC(C2)OC=2C(=CC(=CC=2)C(=O)OC(C)(C)C)N)=C1 ZVUQAXUPDWVVQL-UHFFFAOYSA-N 0.000 description 1
UNNMTKGKCWNQNU-UHFFFAOYSA-N tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C([N+]([O-])=O)C=C1 UNNMTKGKCWNQNU-UHFFFAOYSA-N 0.000 description 1
PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
VXMJEMJQRVMGNS-UHFFFAOYSA-N tert-butyl n-[2-(methylamino)acetyl]carbamate Chemical compound CNCC(=O)NC(=O)OC(C)(C)C VXMJEMJQRVMGNS-UHFFFAOYSA-N 0.000 description 1
JWZVYMQCCBCGLA-UHFFFAOYSA-N tert-butyl n-[4-(azetidin-3-yloxy)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1OC1CNC1 JWZVYMQCCBCGLA-UHFFFAOYSA-N 0.000 description 1
WDNMTCPYOJPZBJ-UHFFFAOYSA-N tert-butyl n-[[4-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazol-2-yl]methyl]-n-methylcarbamate Chemical compound S1C(CN(C)C(=O)OC(C)(C)C)=NC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 WDNMTCPYOJPZBJ-UHFFFAOYSA-N 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical class CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical class OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)
Pyrrole Compounds (AREA)

NO19996208A 1997-06-20 1999-12-15 Nye 2-(iminometyl)amino-fenylderivater, fremstilling og anvendelse derav, samt farmasoytisk preparat NO315321B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9707701A FR2764889B1 (fr)	1997-06-20	1997-06-20	Nouveaux derives du 2-(iminomethyl)amino-phenyle, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant
PCT/FR1998/001250 WO1998058934A1 (fr)	1997-06-20	1998-06-15	Nouveaux derives du 2-(iminomethyl)amino-phenyle, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant

Publications (3)

Publication Number	Publication Date
NO996208D0 NO996208D0 (no)	1999-12-15
NO996208L NO996208L (no)	2000-02-15
NO315321B1 true NO315321B1 (no)	2003-08-18

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ID=9508226

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NO19996208A NO315321B1 (no)	1997-06-20	1999-12-15	Nye 2-(iminometyl)amino-fenylderivater, fremstilling og anvendelse derav, samt farmasoytisk preparat

Country Status (28)

Country	Link
EP (1)	EP0991654B1 (de)
JP (1)	JP2002507965A (de)
KR (2)	KR100618478B1 (de)
CN (1)	CN1195762C (de)
AR (1)	AR012250A1 (de)
AT (1)	ATE297935T1 (de)
AU (1)	AU737964B2 (de)
BR (1)	BR9810197B1 (de)
CA (1)	CA2294809C (de)
CZ (1)	CZ299237B6 (de)
DE (1)	DE69830584T2 (de)
DK (1)	DK0991654T3 (de)
ES (1)	ES2244068T3 (de)
FR (1)	FR2764889B1 (de)
HU (1)	HUP0002425A3 (de)
IL (1)	IL133223A (de)
MY (1)	MY123193A (de)
NO (1)	NO315321B1 (de)
NZ (1)	NZ501656A (de)
PL (1)	PL191987B1 (de)
PT (1)	PT991654E (de)
RU (1)	RU2202543C2 (de)
SK (1)	SK286911B6 (de)
TR (1)	TR199903175T2 (de)
TW (1)	TW422842B (de)
UA (1)	UA70921C2 (de)
WO (1)	WO1998058934A1 (de)
ZA (1)	ZA985392B (de)

Families Citing this family (28)

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Publication number	Priority date	Publication date	Assignee	Title
SE9801990D0 (sv) *	1998-06-04	1998-06-04	Astra Ab	New 3-aryl propionic acid derivatives and analogs
AR019190A1 (es) *	1998-07-08	2001-12-26	Sod Conseils Rech Applic	Derivados de 2-aminopiridinas, productos intermedios para su preparacion, medicamentos y composiciones farmaceuticas que los contienen y su uso para preparar medicamentos
EP1103552A4 (de) *	1998-08-07	2003-01-15	Takeda Chemical Industries Ltd	Benzothiepin-derivate, verfahren zu ihrer herstellung und ihre verwendungen
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1997
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1998
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Also Published As

Publication number	Publication date
PT991654E (pt)	2005-10-31
RU2202543C2 (ru)	2003-04-20
FR2764889B1 (fr)	2000-09-01
ES2244068T3 (es)	2005-12-01
NO996208D0 (no)	1999-12-15
BR9810197A (pt)	2000-08-08
CZ299237B6 (cs)	2008-05-28
CN1195762C (zh)	2005-04-06
DE69830584D1 (de)	2005-07-21
PL191987B1 (pl)	2006-07-31
CZ459799A3 (cs)	2000-07-12
JP2002507965A (ja)	2002-03-12
KR20010013983A (ko)	2001-02-26
FR2764889A1 (fr)	1998-12-24
HK1030218A1 (en)	2001-04-27
IL133223A (en)	2004-09-27
DE69830584T2 (de)	2006-03-16
KR100618478B1 (ko)	2006-09-01
AR012250A1 (es)	2000-09-27
HUP0002425A1 (hu)	2001-11-28
PL337499A1 (en)	2000-08-28
NO996208L (no)	2000-02-15
CN1264385A (zh)	2000-08-23
ZA985392B (en)	1999-01-20
DK0991654T3 (da)	2005-10-17
BR9810197B1 (pt)	2010-02-09
NZ501656A (en)	2001-12-21
EP0991654B1 (de)	2005-06-15
WO1998058934A1 (fr)	1998-12-30
TR199903175T2 (xx)	2000-04-21
KR20050098970A (ko)	2005-10-12
SK286911B6 (sk)	2009-07-06
CA2294809A1 (fr)	1998-12-30
TW422842B (en)	2001-02-21
CA2294809C (fr)	2010-02-02
KR100545946B1 (ko)	2006-01-26
MY123193A (en)	2006-05-31
UA70921C2 (uk)	2004-11-15
IL133223A0 (en)	2001-03-19
AU737964B2 (en)	2001-09-06
ATE297935T1 (de)	2005-07-15
SK179699A3 (en)	2000-05-16
EP0991654A1 (de)	2000-04-12
AU8218998A (en)	1999-01-04
HUP0002425A3 (en)	2001-12-28

Legal Events

Date	Code	Title	Description
2015-01-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
EP0991654B1 (de)	2005-06-15	2-(iminomethyl)aminophenyl-derivate, deren herstellung, verwendung als medikamente und diese enthaltende pharmazeutische zubereitungen
US7553976B2 (en)	2009-06-30	Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
US6586454B2 (en)	2003-07-01	Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them
WO1992003132A1 (en)	1992-03-05	Indole derivatives which inhibit leukotriene biosynthesis
HUP0104013A2 (hu)	2002-04-29	Új N-(iminometil)amin-származékok, előállításuk, alkalmazásuk gyógyszerekként és az ezeket a vegyületeket tartalmazó gyógyászati készítmények
EP1385840B1 (de)	2006-10-04	Sulfonamide
NO324065B1 (no)	2007-08-06	Nye 2-(iminometyl)amino-fenyl-derivater, fremstilling, medikamenter inneholdende disse, farmasoytiske preparater inneholdende disse og anvendelse av disse for fremstilling av medikament
MXPA99011971A (en)	2000-09-04	Novel 2-(iminomethyl)amino-phenyl derivatives, preparation, application as medicines and compositions containing same
FR2911136A1 (fr)	2008-07-11	Derives de n-(4-cyano-1h-pyrazol-3-yl)methylamine substitues leur preparation et leur application en therapeutique.
KR20070018816A (ko)	2007-02-14	제조 방법